10 Best Italy Multiday Tours in September 2026

Explore Malta 7 Days, Self-drive - September 2026

15% OFF TODAY

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Explore Malta 7 Days, Self-drive - September 2026

Trip customizable

Best price guaranteed

Discover the best of Malta during this seven-day self-drive tour! Walk through the streets of La Valletta, often referred to as “the city built by gentlemen for gentlemen”, the capital of Malta offers both culture and relaxation. Visit the famous Mosta Basilica, which is the third-largest in Europe and one of the main highlights of Malta.

Art and architecture

Tour Type

Private Tour

Accommodation

Hotel

Age Range

6-99 yrs

Operated in

english

Destinations

Sliema, St Julian's, Sliema

15% OFF TODAY

Duration7 days

From

USD 612

USD 520

Saving

USD 92

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Tuscany Walking and Wine - September 2026

4.9

(9 reviews )

No booking fees

Best price guaranteed

Want to explore Tuscany without a rushed itinerary? Want a small group? Want to hike to wineries and hill towns? Stay in interesting hotels that are hundreds of years old? A wine and food buff? Then this is for you. I had a great time on this trip. Had a full day in Sienna and a nice orientation tour of Florence (I spent a few extra days) Plus to get to visit lesser known towns that the big companies overlook. My favorite was Pienza. A nice little town that also had my favorite hotel and great places to eat. And yes, we tasted wonderful Italian wines, as well as the best cold cuts and cheeses I’ve ever tasted. And did I also mention hiking to wineries and hill towns? Wonderful sights, with spectacular views. One hike it rained towards the end, but that didn’t dampen our spirits.

Walking tours

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

16-99 yrs

Operated in

english

Destinations

Florence, Pisa, San Gimignano, T

Florence, Pisa, San Gimignano, Tuscany, Pienza, Montalcino

Duration8 days

From

USD 2,830

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Walk The Prosecco Hills & Hidden Venice - September 2026

4.8

(77 reviews )

No booking fees

Best price guaranteed

Walking on this holiday is varied and well within most people's grasp. Aside from the rolling hills of Prosecco vineyards it includes forest walking and following along side a river. The hotel is most comfortable with large airy bedrooms and updated bathrooms which do not detract from the historic building. It sits within its own grounds including a large swimming pool and a bookable spa. The village of Soligo is small with 3 cafe's and a small shop which stocks a wide range of biscuits, soft drinks and bottled water. There is one sure thing about this holiday and this is you will not go hungry. Lunches are freshly made by the local shop and will keep you going during the walks. The hotel food is second to none and the other resturants we eat at also supplied delicous food. The highlight of this trip is Prosecco in all its forms. I learnt a lot about how the wine was made and how to tell one bottle from another.

Trekking and HikingFood tours

Tour Type

Small Group Tour

Accommodation

Hotel, Villa

Age Range

18-99 yrs

Operated in

english

Destinations

Venice, Treviso, Pieve Di Cadore

Venice, Treviso, Pieve Di Cadore, Cison Di Valmarino, Asolo, Conegliano, Pieve Di Soligo

Duration8 days

From

USD 2,820

USD 2,735

Saving

USD 85

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Italian Scene - September 2026

4.6

(57 reviews )

No booking fees

Best price guaranteed

The scenery was beautiful. Next time I'd slow it down a bit though and enjoy each city for a few days.

Countryside and village visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Bay Of Naples, Assisi, Ven

Rome, Bay Of Naples, Assisi, Venice, Milan, Florence

Duration10 days

From

USD 1,795

USD 1,741

Saving

USD 54

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Sicily & Amalfi Coast Escape - September 2026

Trip customizable

Best price guaranteed

A trip from Sorrento to Sicily promises a journey filled with scenic beauty, rich history, and vibrant culture. Explore the wonders of the Amalfi Coast, and Sicily on an Italian adventure from Rome! Walk the ruins of Pompeii, soak up the atmosphere along the Sorrentine Coast, and sun-bleached Capri. Discover the Mediterranean island of Sicily through its unique architecture, charming villages, and traditional cuisine. Stroll through endless stretches of stunning beaches and explore the majestic ancient ruins of past empires!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

7-99 yrs

Operated in

english

Destinations

Amalfi Coast & Campania, Sorrent

Amalfi Coast & Campania, Sorrento, Palermo, Rome, Taormina, Agrigento, Sicily

Duration11 days

From

USD 3,073

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17% OFF TODAY

Classic Europe - September 2026

4.8

(70 reviews )

No booking fees

Best price guaranteed

This tour was an amazing experience and a great way to see A LOT of Europe in a short amount of time. The trip was fast paced but very well planned out with the itinerary and mix of activities that you see and do. Jemma, our tour guide was absolutely amazing! We couldn't have asked for better! She was charismatic, funny, knowledgeable, organized, and guided us in a positive way where we got the very most out of the travel experience learning the local history, foods, culture and best site seeing spots. She went above and beyond to make sure we were getting the most out of our tour experience. Gabriel, our driver was also phenomenal. We always felt very safe and he was always perfectly punctual and helped us load/ unload and kept us very comfortable on the coach.

Active and outdoor

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Paris, Rome, London, Amsterdam

Paris, Rome, London, Amsterdam, Nuremberg, Beaune, Montecatini Terme, Venice

17% OFF TODAY

Duration14 days

From

USD 3,650

USD 3,015

Saving

USD 635

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Treasures of Naples & the Amalfi Coast - September 2026

Trip customizable

Best price guaranteed

From Rome, travel to Naples and see the treasures of the ancient city. Stop at the legendary site of Pompeii which was completely destroyed 2,000 years ago in the catastrophic eruption of Mount Vesuvius. Discover Positano, one of Italy's crown jewels, with stunning scenery and colourful cliffside villas. Set sail for the idyllic Italian island of Capri on a full-day tour and relax at the charming town of Sorrento on your Amalfi Coast escape with plenty of free time to explore on your own

BeachArt and architecture

Tour Type

Small Group Tour

Accommodation

Hotel

Age Range

13-99 yrs

Operated in

english

Destinations

Rome, Lazio, Naples, Sorrento, Amalfi

Duration6 days

From

USD 2,132

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Cycling Puglia & Matera - September 2026

4.7

(66 reviews )

No booking fees

Best price guaranteed

Perfect spring cycling, beautiful scenery, wonderful food

Bicycle tours

Tour Type

Small Group Tour

Accommodation

Hotel, Resort

Age Range

16-99 yrs

Operated in

english

Destinations

Matera, Salento, Alberobello, Os

Matera, Salento, Alberobello, Ostuni, Avetrana, Gallipoli, Otranto, Lecce

Duration8 days

From

USD 3,000

USD 2,910

Saving

USD 90

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Discovery of Italy: 8 Days - September 2026

4.5

(2 reviews )

Trip customizable

Best price guaranteed

I have had the wonderful pleasure of touring with you, the tour was well executed. The experiences are amazing and very unique. So much fun and I will tour again. I will recommend.

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel

Age Range

1-99 yrs

Operated in

english

Destinations

Rome, Florence, Venice, The Vati

Rome, Florence, Venice, The Vatican, Assisi, Montepulciano, Siena, Tuscany, Bologna, Padua

Duration8 days

From

USD 2,750

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8% OFF TODAY

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Italian Intermezzo - September 2026

4.7

(65 reviews )

No booking fees

Best price guaranteed

This tour is the BEST way to see all the infamous spots in Italy, plus local hidden gems, at a reasonable cost and if you are short on time (we had a school break time limitation). It covered everything! We budgeted for the add-ons, especially those with meals, but you could choose to have more free time if you wanted. The food was extraordinary, the bus was roomy and immaculately clean, our driver Antonello was superb, and our Travel Director Anneleis was amazing! She was so talented at integrating the tour highlights, guests, keeping it fun even in the rainy weather, knowledgeable, and able to troubleshoot anything to ensure we had the best experience of a lifetime!! I would love to go back and explore Southern Italy next. The hotels were elegant (only one was just "OK" only because it was in need of some renovations) and the service with our luggage, tipping, etc. was seamless. I highly recommend the Italian Intermezzo tour and Insight Vacations. Favoloso!

Cultural, religious and historic sites

Tour Type

Group Tour

Accommodation

Hotel, Villa

Age Range

5-99 yrs

Operated in

english

Destinations

Milan, Rome, Venice, Florence

8% OFF TODAY

Duration8 days

From

USD 3,225

USD 2,973

Saving

USD 252

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18% OFF TODAY

European Vistas - September 2026

4.8

(51 reviews )

No booking fees

Best price guaranteed

We wished we could have longer time at Belgian . We were given 1 hour and 30 minutes to do so many things. Listened to the guide s orientation, find and queue up for foods, wait for the foods to be served then take some time to chew the foods, take some photos of that beautiful architecture buildings, queue up for WC. Then not enough to shop at that area.

Natural landmarks sightseeing

Tour Type

Group Tour

Accommodation

Hotel

Age Range

10-99 yrs

Operated in

english

Destinations

Amsterdam, Brussels, Rhine, Inns

Amsterdam, Brussels, Rhine, Innsbruck, Verona, Lucerne, Burgundy, Paris

18% OFF TODAY

Duration8 days

From

USD 1,805

USD 1,475

Saving

USD 330

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5% OFF TODAY

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Treasures of Italy - September 2026

4.8

(88 reviews )

No booking fees

Best price guaranteed

It was a fast paced trip. It is a bit difficult staying only one night in a few places, just the logistics of packing up several nights and having everything ready for the next day is challenging. But, that being said I thoroughly enjoyed seeing so many things through out Italy. That inconvenience was minor in comparison to the amount of ground we covered.

Museum and gallery visits

Tour Type

Group Tour

Accommodation

Hotel, Resort

Age Range

5-99 yrs

Operated in

english

Destinations

Rome, Venice

5% OFF TODAY

Duration11 days

From

USD 5,125

USD 4,894

Saving

USD 231

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Walking in Sardinia - September 2026

4.6

(57 reviews )

No booking fees

Best price guaranteed

For anyone with coeliac disease, this trip is perfection. You get wonderful food, and lots of it. I managed to put on weight in spite of the energy expenditure, which was considerable!

Trekking and Hiking

Tour Type

Small Group Tour

Accommodation

Hotel, Hut

Age Range

16-99 yrs

Operated in

english

Destinations

Sardinia, Dorgali, Gulf Of Orose

Sardinia, Dorgali, Gulf Of Orosei, Gorropu Gorge, Serra Orrios, Bue Marino Grotto, Tiscali

Duration8 days

From

USD 2,550

USD 2,474

Saving

USD 77

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Private Gourmet Wine Tour in Tuscany - September 2026

4.5

(2 reviews )

Trip customizable

Best price guaranteed

What a beautiful time spent in Tuscany on this trip. This was a wonderful tour. Great accommodations! Fabulous wines and meals. We had a wonderful driver, Brando, who was patient and knowledgeable. This is a trip well worth it. Villa Lecchi was elegant and made us feel very special! Spectacular location in the heart of Chianti hills

Food toursWine tasting tours

Tour Type

Private Tour

Accommodation

Hotel

Age Range

22-89 yrs

Operated in

english, german

Destinations

Tuscany, Chianti, Florence, Sien

Tuscany, Chianti, Florence, Siena, Pisa

Duration4 days

From

USD 2,846

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Combine Italy in September with Nearby Countries for an Unforgettable Trip

See tours with itineraries going through multiple countries, including Italy

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Alternatively, explore tours that are exclusively just Italy and Spain, Germany and Italy or France and Italy.

All Italy Tours in September 2026

Page 3 of 287 Trips in Italy during September 2026 with 6,301 Reviews

See Italy tours by duration

Explore Malta 7 Days, Self-drive - September 2026

Tuscany Walking and Wine - September 2026

Walk The Prosecco Hills & Hidden Venice - September 2026

Italian Scene - September 2026

Sicily & Amalfi Coast Escape - September 2026

Classic Europe - September 2026

Treasures of Naples & the Amalfi Coast - September 2026

Cycling Puglia & Matera - September 2026

Discovery of Italy: 8 Days - September 2026

Italian Intermezzo - September 2026

European Vistas - September 2026

Treasures of Italy - September 2026

Walking in Sardinia - September 2026

Private Gourmet Wine Tour in Tuscany - September 2026

Page 3 of 287 Trips in Italy during September 2026 with 6,301 Reviews

Combine Italy in September with Nearby Countries for an Unforgettable Trip

Europe

Asia

South America

Africa

North America

Oceania

Polar

Food, wine, events and nightlife

Adventure and sport

Wildlife, landscapes and nature

Boat tours, water sports and marine wildlife

Sightseeing, attractions, culture and history

Air tours, road trips and transfers

Beach, romance, getaways and relaxation

Special interests and hobbies

All Italy Tours in September 2026

Page 3 of 287 Trips in Italy during September 2026 with 6,301 Reviews

See Italy tours by duration

Page 3 of 287 Trips in Italy during September 2026 with 6,301 Reviews